CN112912375A - Novel compound and organic light emitting device comprising same - Google Patents
Novel compound and organic light emitting device comprising same Download PDFInfo
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- CN112912375A CN112912375A CN202080005711.1A CN202080005711A CN112912375A CN 112912375 A CN112912375 A CN 112912375A CN 202080005711 A CN202080005711 A CN 202080005711A CN 112912375 A CN112912375 A CN 112912375A
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- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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Abstract
The present invention provides a novel compound and an organic light emitting device including the same.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2019-0061426, 24, 2019 and korean patent application No. 10-2020-0061908, 22, 5, 2020, the entire contents of which are incorporated herein by reference.
The present invention relates to a novel compound and an organic light emitting device using the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
An organic light emitting device generally has a structure including an anode and a cathode, and an organic layer between the anode and the cathode. In order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, which emit light when they transition to the ground state again.
For organic materials used for the organic light emitting devices as described above, development of new materials is continuously demanded.
Documents of the prior art
Patent document
(patent document 0001) Korean patent laid-open publication No. 10-2013-073537
Disclosure of Invention
Technical subject
The present invention relates to an organic light emitting device including the novel compound.
Means for solving the problems
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-described chemical formula 1,
X1、X2and X3Each independently is N or CH, however, X1、X2And X3One or more of them is N,
y is O, S or NR'1Here, R'1Is substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
L1and L2Each independently is a direct bond; substituted or unsubstituted C6-60An arylene group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S5-60A heteroarylene group, a heteroaryl group,
R1each independently is hydrogen, deuteriumOr substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
ra is any one selected from the group consisting of,
R2each independently hydrogen, deuterium, or substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
R3is substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
each n is independently an integer of 0 to 7,
m is an integer of 0 to 8,
p is an integer of 0 to 5,
a is an integer of 0 to 4.
In addition, the present invention provides an organic light emitting device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound of the present invention.
Effects of the invention
The compound represented by the above chemical formula 1 may be used as a material of an organic layer of an organic light emitting device in which improvement in efficiency, lower driving voltage, and/or improvement in lifetime characteristics may be achieved. In particular, the compound represented by the above chemical formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 3, an electron transport layer 8, an electron injection layer 9, and a cathode 4.
Detailed Description
Hereinafter, the present invention will be described in more detail to assist understanding thereof.
(definition of wording)
In the context of the present specification,
represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means substituted with a substituent selected from deuterium (D); a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio radicals (A), (B), (C), (D), (
alkyl thio xy); arylthio radicals (A), (B), (C
aryl thio xy); alkylsulfonyl (
alkyl sulfoxy); arylsulfonyl (
aryl sulfoxy); a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or 1 or more substituents of 1 or more heterocyclic groups containing N, O and S atoms, or substituted or unsubstituted by 2 or more substituents of the above-exemplified substituents being bonded. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there may be mentioned, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a triphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,
And a fluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above-mentioned fluorenyl group is substituted, it may be
And the like. But is not limited thereto.
In the present specification, the heterocyclic group is a heterocyclic group containing 1 or more of O, N, Si and S as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolylBenzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinophthalone
Azolyl group,
Oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the above-mentioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned alkyl group. In the present specification, the heteroaryl group in the heteroarylamine can be applied to the above description about the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as exemplified above for the alkenyl group. In the present specification, the arylene group is a 2-valent group, and in addition thereto, the above description about the aryl group can be applied. In the present specification, a heteroarylene group is a 2-valent group, and in addition to this, the above description about a heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic group is not a 1-valent group but a combination of 2 substituents, and in addition to this, the above description on the heterocyclic group can be applied.
(Compound (I))
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-described chemical formula 1,
d is a radical of deuterium,
X1、X2and X3Each independently is N or CH, however, X1、X2And X3One or more of them is N,
y is O, S or NR'1Here, R'1Is substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
L1and L2Each independently is a direct bond; substituted or unsubstituted C6-60An arylene group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S5-60A heteroarylene group, a heteroaryl group,
R1each independently hydrogen, deuterium, or substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
ra is any one selected from the group consisting of,
R2each independently hydrogen, deuterium, or substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
R3is substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
each n is independently an integer of 0 to 7,
m is an integer of 0 to 8,
p is an integer of 0 to 5,
a is an integer of 0 to 4.
Preferably, L1And L2Each independently being a direct bond or a phenylene group.
Preferably, R'1Phenyl substituted or unsubstituted with more than one deuterium.
Preferably, R1Each independently is hydrogen, deuterium, or phenyl substituted or unsubstituted with more than one deuterium.
Preferably, R2Each independently is hydrogen, deuterium, or phenyl substituted or unsubstituted with more than one deuterium.
Preferably, R3Phenyl substituted or unsubstituted with more than one deuterium.
In the case where the terminal substituent of the compound represented by the above chemical formula 1 is further substituted with deuterium (D), the lifetime characteristics can be improved when applied to an organic light emitting device, and thus it is preferable.
Preferably, the compound represented by the above chemical formula 1 is any one selected from the group consisting of:
the compound represented by the above chemical formula 1 can be produced by the following reaction formula a.
[ reaction formula A ]
In the above reaction formula A, except Z1And Z2The other groups are as defined above, Z1And Z2Each independently is a halogen, for example bromine or chlorine.
The reactants, catalyst, solvent and the like used in the reaction formula a may be appropriately changed depending on the target product. The method for producing the compound of chemical formula 1 can be further embodied in the production examples described below.
(organic light emitting device)
In addition, the present invention provides an organic light emitting device comprising the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light emitting device, comprising: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers include a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller number of organic layers may be included.
In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport, and the hole injection layer, the hole transport layer, or the layer simultaneously performing hole injection and transport includes the compound represented by the above chemical formula 1.
In addition, the organic layer may include an electron inhibiting layer including the compound represented by the chemical formula 1.
In addition, the organic layer may include a light emitting layer including the compound represented by the chemical formula 1.
In addition, the organic layer may include an electron transport layer, an electron injection layer, or a layer simultaneously performing electron transport and electron injection, and the electron transport layer, the electron injection layer, or the layer simultaneously performing electron transport and electron injection includes the compound represented by the above chemical formula 1.
In addition, the organic light emitting device according to the present invention may be an organic light emitting device of a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an inverted (inverted type) organic light emitting device in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be included in the above light emitting layer.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 3, an electron transport layer 8, an electron injection layer 9, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in 1 or more layers among the above hole injection layer, hole transport layer, electron suppression layer, light emitting layer, electron transport layer, and electron injection layer.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that 1 or more of the above organic layers include the compound represented by the above chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, the following production can be performed: the organic el display device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.
In addition, the compound represented by the above chemical formula 1 may be used not only for forming an organic layer by a vacuum evaporation method but also for forming an organic layer by a solution coating method in the manufacture of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device may be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.
In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO Al or SNO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO2And a multilayer structure material such as Al, but not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: a compound having an ability to transport holes, having an effect of injecting holes from an anode, having an excellent hole injection effect for a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and having an excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport substance is a substance that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The electron-inhibiting layer is a layer interposed between the hole-transporting layer and the light-emitting layer in order to prevent electrons injected from the cathode from being transferred to the hole-transporting layer without being recombined in the light-emitting layer, and is also referred to as an electron-blocking layer. In the electron-suppressing layer, a substance having a smaller electron affinity than that of the electron-transporting layer is preferably used.
The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds
Pyrimidine derivatives, etc., but are not limited thereto.
As the dopant material, there are an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, or the like having an arylamino group,
Diindenopyrene, and the like, and styrylamine compounds are compounds in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted with 1 or 2 or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can favorably receive electrons from the cathode and transfer the electrons to the light emitting layer, and is preferably a substance having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium and samarium, and in each case accompanied by an aluminum or silver layer.
The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: has the ability to transport electrons, has the effect of injecting electrons from the cathode, and has excellent electron injection to the light-emitting layer or the light-emitting materialAnd a compound which prevents excitons generated in the light-emitting layer from migrating to the hole-injecting layer and which has excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
In addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting device.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device comprising the same will be specifically described in the following examples. However, the following examples are provided to illustrate the present invention, and the scope of the present invention is not limited thereto.
[ production example ]
Production example 1-1: synthesis of Compound A2
1) Production of Compound A1
4-chlorodibenzothiophene (100g, 0.45mol) and 300ml of acetic acid were charged in a 1000ml round-bottomed flask under a nitrogen atmosphere, bromine (73.1g, 0.47mol) was slowly added thereto at a low temperature by means of a funnel (dropping funnel), and then stirred at room temperature for 15 hours. Then, the solid obtained by filtration was dissolved in tetrahydrofuran, washed with water and a solution of sodium thiosulfate, the organic layer was separated and recrystallized from ethanol to obtain intermediate A1(85g, yield 62%, MS: [ M + H ] was obtained]+＝296)。
2) Production of Compound A2
After compound A1(85.0g, 285.6mmol) was dissolved in tetrahydrofuran (850mL), the temperature was lowered to-78 deg.C and 2.5M t-butyllithium (t-BuLi) (115.4mL, 288.5mmol) was added slowly. After stirring at the same temperature for 1 hour, triisopropyl borate (98.9mL, 428.4mmol) was added, and the temperature was slowly raised to room temperature and stirred for 2.5 hours. To the reaction mixture was added 2N aqueous hydrochloric acid (900mL), and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed with water and ethyl acetate (ethyl ether) in this order, and dried under vacuum to give Compound A2(68.1g, yield 91%, MS: [ M + H ])]+＝263)。
Production examples 1 and 2: synthesis of Compound A3
1) Production of Compound A3-1
A2(20g, 76.2mmol) and 2-chloro-benzo under nitrogen atmosphere
Oxazole (11.7g, 76.2mmol) was added to 600ml of 1, 4-bis
In an alkane, stirring and refluxing. Cesium carbonate (74.5g, 228.6mmol) was dissolved in 74ml of water and charged, and after sufficiently stirring, the cesium carbonate was chargedBis (tri-tert-butylphosphino) palladium (0.8g, 1.5 mmol). After 5 hours of reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was put into 1279mL of chloroform and dissolved, and washed with water 2 times, then the organic layer was separated, anhydrous magnesium sulfate was added, and after stirring, filtration was performed, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give white solid compound A3-1(21.7g, 85%, MS: [ M + H ]]+＝336.8)。
2) Production of Compound A3
A3-1(21.7g, 64.6mmol) and bis (pinacolato) diboron (19.7g, 77.5mmol) were added to 434ml of bis under nitrogen
In an alkane (Diox), stirred and refluxed. Then, potassium acetate (18.6g, 193.9mmol) was charged, and after sufficiently stirring, bis (dibenzylideneacetone) palladium (0) (1.1g, 1.9mmol) and tricyclohexylphosphine (1.1g, 3.9mmol) were charged. After 4 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer was filtered to remove the alkali, and the filtered organic layer was distilled. The obtained substance was again charged into 828mL of chloroform and dissolved, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to give an ivory-colored solid compound A3(21.5g, 78%, MS: [ M + H ]]+＝428.1)。
Production examples 1 to 3: synthesis of Compound A4
Using 2-chlorobenzothiazole instead of 2-chlorobenzo
Except for azole, compound a4 was produced in the same manner as in the production of compound A3 of production example 1-2.
Production examples 1 to 4: synthesis of Compound A5
Using 2-chloro-1-phenyl-1H-benzimidazole instead of 2-chlorobenzo
Except for azole, compound a5 was produced in the same manner as in the production of compound A3 of production example 1-2.
Production examples 1 to 5: synthesis of Compound A6
Use of 2- (3-bromophenyl) benzothiazole instead of 2-chlorobenzo
Except for azole, compound a6 was produced in the same manner as in the production of compound A3 of production example 1-2.
Production examples 1 to 6: synthesis of Compound A7
Using 2- (4-bromophenyl) benzo
Azole in place of 2-chlorobenzo
Except for azole, compound a7 was produced in the same manner as in the production of compound A3 of production example 1-2.
[ examples ]
Example 1: production of Compound 1
Compound A3(5g, 11.7mmol) and 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl l-1,3, 5-triazine (4.2g, 11.7mmol) are added to 125ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (4.9g, 35.1mmol) was dissolved in 5ml of water and charged, and after sufficiently stirring, bis (tri-tert-butylphosphino) palladium (0.2g, 0.4mmol) was charged. After 7 hours of reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was put into 364mL of tetrahydrofuran and dissolved, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from tetrahydrofuran and ethyl acetate to produce compound 1(6g, 82%, MS: [ M + H ] + ═ 623.1) as a white solid.
Example 2: production of Compound 2
Compound 2(6.3g, yield 85%, MS: [ M + H ] was prepared in the same manner as in preparation of Compound 1 in example 1 except that 2-chloro-4- (dibenzofuran-4-yl) -6-phenyl-1, 3, 5-triazine was used in place of 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine]+＝639)。
Example 3: production of Compound 3
Compound 3(7.3g, yield 89%, MS: [ M + H ] was prepared in the same manner as in preparation of Compound 1 in example 1 except that 2- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9-phenyl-9H-carbazole was used in place of 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl l-1,3, 5-triazine]+＝698)。
Example 4: production of Compound 4
Compound 4(6.6g, yield 81%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound 1 in example 1 except that 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -4-phenyl-9H-carbazole was used in place of 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine]+＝698)。
Example 5: production of Compound 5
Compound 5(6.0g, yield 83%, MS: [ M + H ] was produced in the same manner as in production of Compound 1 in example 1 except that Compound A4 and 2-chloro-4- (dibenzofuran-3-yl) -6-phenyl-1, 3, 5-triazine were used in place of Compound A3 and 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine]+＝639)。
Example 6: production of Compound 6
Compound 6(5.7g, yield 77%, MS: [ M + H ]: M + H ] was produced by the same method as that of production of compound 1 of example 1, except that compound A4 and 2-chloro-4- (dibenzothiophen-4-yl) -6- (phenyl-d 5) -1,3, 5-triazine were used in place of compound A3 and 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine]+＝660)。
Example 7: production of Compound 7
A compound was produced by the same method as the production of compound 1 of example 1 except that compound a4 and 3- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9-phenyl-9H-carbazole were used instead of compound A3 and 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine7(6.0g, yield 75%, MS: [ M + H ]]+＝714)。
Example 8: production of Compound 8
Compound 8(5.7g, yield 71%, MS: [ M + H ]: M + H-carbazole, etc.) was prepared in the same manner as in example 1 except that compound A4 and 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -4-phenyl-9H-carbazole were used in place of compound A3 and 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine]+＝714)。
Example 9: production of Compound 9
Compound 9(5.3g, yield 66%, MS: [ M + H ] was produced in the same manner as in the production of Compound 1 in example 1, except that Compound A4 and 2- (3-chlorophenyl) -4- (dibenzofuran-4-yl) -6-phenyl-1, 3, 5-triazine were used in place of Compound A3 and 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine]+＝715)。
Example 10: production of Compound 10
Compound 10(4.5g, yield 65%, MS: [ M + H ]: M + H ] was produced in the same manner as in the production of Compound 1 in example 1, except that Compound A5 and 2-chloro-4- (dibenzofuran-1-yl) -6-phenyl-1, 3, 5-triazine were used in place of Compound A3 and 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine]+＝698)。
Example 11: production of Compound 11
Compound 11(4.3g, yield 61%, MS: [ M + H ]: M + H) was produced in the same manner as in the production of Compound 1 in example 1, except that Compound A5 and 2-chloro-4- (dibenzothiophen-2-yl) -6-phenyl-1, 3, 5-triazine were used in place of Compound A3 and 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine]+＝714)。
Example 12: production of Compound 12
Compound 12(5.4g, yield 70%, MS: [ M + H ]: M + H-carbazole, etc.) was prepared in the same manner as in the preparation of Compound 1 of example 1, except that Compound A5 and 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -2-phenyl-9H-carbazole were used in place of Compound A3 and 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine]+＝773)。
Example 13: production of Compound 13
Compound 13(5.1g, yield 66%, MS: [ M + H ] (M + H): 13) was produced by the same method as that of production of compound 1 of example 1, except that compound A5 and 4- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9-phenyl-9H-carbazole were used in place of compound A3 and 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine]+＝773)。
Example 14: production of Compound 14
In addition to using compound a6 and 2-chloro-4- (dibenzofuran-4-yl) -6- (phenyl-d 5) -1,3, 5-triazine instead of compound A3 and 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine, the procedure was repeated as in example 1Production of Compound 1 Compound 14(5.2g, yield 75%, MS: [ M + H ]]+＝720)。
Example 15: production of Compound 15
Compound 15(5.1g, yield 74%, MS: [ M + H ] was produced in the same manner as in the production of Compound 1 in example 1 except that Compound A6 and 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole were used in place of Compound A3 and 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine]+＝714)。
Example 16: production of Compound 16
Compound 16(5.1g, yield 67%, MS: [ M + H ] was produced by the same method as that of production of Compound 1 in example 1 except that Compound A6 and 9- (4- (3-chlorophenyl) -6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole were used in place of Compound A3 and 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine]+＝790)。
Example 17: production of Compound 17
Compound 17(4.7g, yield 68%, MS: [ M + H ]: M + H) was produced in the same manner as in the production of Compound 1 in example 1, except that Compound A7 and 2-chloro-4- (dibenzofuran-4-yl) -6-phenyl-1, 3, 5-triazine were used in place of Compound A3 and 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine]+＝699)。
Example 18: preparation of Compound 18
Compound 18(4.9g, yield 70%, MS: [ M + H ] was produced by the same method as the production of Compound 1 of example 1 except that Compound A7 and 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole-1, 3,4,5,6,8-d6 were used in place of Compound A3 and 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine]+＝704)。
Example 19: production of Compound 19
Compound 19(5.0g, yield 65%, MS: [ M + H ]: Compound 19) was produced by the same method as that of production of Compound 1 of example 1, except that Compound A7 and 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -3-phenyl-9H-carbazole were used in place of Compound A3 and 2-chloro-4- (dibenzofuran-2-yl) -6-phenyl-1, 3, 5-triazine]+＝774)。
[ Experimental example ]
Experimental example 1
Indium Tin Oxide (ITO) and a process for producing the same
The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared, the following hexanitrile hexaazatriphenylene (hexanit) was addedAle hexaazatriene, HAT) compounds and their use
The hole injection layer is formed by thermal vacuum deposition. On the above hole injection layer, an HT-1 compound is added
Is subjected to thermal vacuum evaporation, and HT-2 compounds are sequentially added to
The hole transport layer is formed by vacuum evaporation. Then, compound 1 produced as a host, the following H1 compound, and phosphorescent dopant GD were co-evaporated at a weight ratio of 47:47:6 on the hole transport layer to form
A thick light emitting layer. On the above-mentioned luminescent layer an ET-1 substance is added
Is formed by vacuum evaporation to a thickness of (1) to (1) and vacuum evaporation is performed to an ET-2 substance and LiQ (Lithium Quinolate) on the hole blocking layer to form a hole blocking layer
The electron transport layer of (1). On the electron transport layer, sequentially
Lithium fluoride (LiF) is evaporated to a thickness, and then deposited thereon
Aluminum is evaporated to a thickness to form a cathode.
In the above process, the evaporation speed of the organic material is maintained
Lithium fluoride maintenance of cathode
Deposition rate of (3), aluminum maintenance
The vacuum degree is maintained at 1X 10 during the vapor deposition-7To 5X 10-8And (4) supporting.
Experimental examples 2 to 19
Organic light-emitting devices of experimental examples 2 to 19 were produced in the same manner as in experimental example 1 except that compounds shown in table 1 below were used as hosts instead of compound 1 in forming the light-emitting layer.
Comparative Experimental examples 1 to 3
Organic light-emitting devices of comparative examples 1 to 3 were produced in the same manner as in experimental example 1, except that compounds 1 were replaced with C1 to C3 described below as hosts in the formation of the light-emitting layer, respectively, as shown in table 1 below.
The organic light emitting devices fabricated in the above experimental examples 1 to 19 and comparative examples 1 to 3 were applied with current, and the voltage, efficiency and lifetime were measured, and the results thereof are shown in the following table 1. T95 refers to the time required for the luminance to decrease from the initial luminance to 95%.
[ Table 1]
As shown in table 1 above, it was confirmed that in the case of the organic light emitting device manufactured using the compound according to the present invention as a host of the light emitting layer, the efficiency and the life characteristics were excellent as compared with the organic light emitting device of the comparative example.
In particular, it was confirmed that the organic light emitting device according to the example had an efficiency increased by about 10% and a lifetime increased by about 20 to 50% as compared with the compound C1 which is a phosphorescent host material generally used.
The effect of the triazine substituted on dibenzothiophene significantly varies depending on the presence or absence of an additional substituent when applied to an organic light emitting device, and it was confirmed that comparative experiment example 2 using a compound containing no additional substituent had a higher driving voltage and a lower lifetime characteristic than the examples of the present application.
Further, depending on the substitution position of the substituent, the effect difference was significant when applied to an organic light emitting device, and it was confirmed that the efficiency and the lifetime characteristics were significantly reduced in comparative experiment example 3 using a compound having a different substituent position than the compound of the present invention having a triazine substituent at the No. 4 position of dibenzothiophene.
In comparison of device examples using compounds 8 and 16 which are compounds of the present invention, it was confirmed that comparative experiment example 3 shows large differences in voltage, efficiency and lifetime depending on the kind and substitution position of the linker, although there is no large difference in efficiency and lifetime depending on the presence or absence of the phenyl linker.
Further, it is confirmed that the lifetime characteristics are improved in the case where the terminal is deuterium, as compared with experimental examples 18 to 19.
As described above, it was confirmed that the compound of the present invention showed superior characteristics in terms of efficiency and lifetime depending on the position of the substituent and the kind of the substituent, as compared with the comparative example compound.
Description of the symbols
1: substrate 2: anode
3: light-emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: electron suppression layer 8: electron transport layer
9: an electron injection layer.
Claims (12)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1, the first and second organic solvents,
X1、X2and X3Each independently is N or CH, however, X1、X2And X3One or more of them is N,
y is O, S or NR'1Here, R'1Is substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
L1and L2Each independently is a direct bond; substituted or unsubstituted C6-60An arylene group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S5-60A heteroarylene group, a heteroaryl group,
R1each independently hydrogen, deuterium, or substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
ra is any one selected from the group consisting of,
R2each independently hydrogen, deuterium, or substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
R3is substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
each n is independently an integer of 0 to 7,
m is an integer of 0 to 8,
p is an integer of 0 to 5,
a is an integer of 0 to 4.
2. The compound of claim 1, wherein L1And L2Each independently being a direct bond or a phenylene group.
3. The compound of claim 1, wherein R'1Phenyl substituted or unsubstituted with more than one deuterium.
4. The compound of claim 1, wherein R1Each independently is hydrogen, deuterium, or phenyl substituted or unsubstituted with more than one deuterium.
5. The compound of claim 1, wherein R2Each independently is hydrogen, deuterium, or phenyl substituted or unsubstituted with more than one deuterium.
6. The compound of claim 1, wherein R3Phenyl substituted or unsubstituted with more than one deuterium.
7. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:
8. an organic light emitting device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound according to any one of claims 1 to 7.
9. The organic light-emitting device according to claim 8, wherein the organic layer containing the compound is a light-emitting layer.
10. The organic light-emitting device according to claim 9, wherein the compound is contained as a host.
11. An organic light-emitting device according to claim 9 wherein the light-emitting layer further comprises a dopant compound.
12. The organic light-emitting device according to claim 8, wherein the organic layer containing the compound is an electron injection layer, an electron transport layer, or a layer in which electron injection and electron transport are performed simultaneously.
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| CN106316925A (en) * | 2015-06-26 | 2017-01-11 | 上海和辉光电有限公司 | Organic electroluminescence compound and application thereof |
| KR20180028179A (en) * | 2016-09-08 | 2018-03-16 | 에스케이케미칼 주식회사 | Compound for organic electroluminescent device and organic electroluminescent device comprising the same |
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